Methanol → HCID 178493705, compound

HRID 1019717Notes

Reaction equation

HRID 1019717 reaction equation
CO.CN1[C:8](=[O:9])CCC1.[H-].[Na+].Br[C:13]1[N:18]=[C:17]2[N:19]([C@H:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH3:24])[C:20]([OH:22])=[N:21][C:16]2=[N:15][CH:14]=1>CCOC(C)=O>[CH3:8][O:9][C:13]1[N:18]=[C:17]2[N:19]([C@H:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH3:24])[C:20]([OH:22])=[N:21][C:16]2=[N:15][CH:14]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 13387N-methyl-2-pyrrolidoneHCID 24758Sodium hydrideHCID 178461678HCID 178461678, compound

Product 1

HCID 178493705HCID 178493705, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

A thick-walled microwave bottle equipped with a stirbar was charged with MeOH (2.0 equiv) and NMP (20 volume equivalents). To the resulting solution was added NaH (2.0 equiv), resulting in gas evolution. (S)-6-Bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2-ol (1.0 equiv) was then added to the reaction, and the resulting mixture was immediately fitted with a septum and cap and heated to 200° C. in a microwave for 30 min. The reaction was then diluted with EtOAc, washed twice with saturated aq. NaHCO3 and once with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Reverse-phase preparative HPLC provided the title compound (29%) as a white solid. LCMS m/z (APCI)=271.1 (M+H).

Workup

  1. customA thick-walled microwave bottle equipped with a stirbar
  2. customresulting in gas evolution
  3. customthe resulting mixture was immediately fitted with a septum
  4. customcap
  5. washwashed twice with saturated aq. NaHCO3 and once with brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a96f602cd18047e7a28312916bce8300
Source dataset
uspto-grants-2014_05
Patent number
US08716291B2

Reaction notes

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